SU952102A3 - Способ получени 0-металлилоксифенола - Google Patents
Способ получени 0-металлилоксифенола Download PDFInfo
- Publication number
- SU952102A3 SU952102A3 SU792782748A SU2782748A SU952102A3 SU 952102 A3 SU952102 A3 SU 952102A3 SU 792782748 A SU792782748 A SU 792782748A SU 2782748 A SU2782748 A SU 2782748A SU 952102 A3 SU952102 A3 SU 952102A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- saturated
- water
- pyrocatechol
- alkyl
- aliphatic
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 18
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims abstract description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 8
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 125000001453 quaternary ammonium group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- 229910001510 metal chloride Inorganic materials 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 3
- 230000003993 interaction Effects 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 150000005826 halohydrocarbons Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 9
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 239000003054 catalyst Substances 0.000 abstract description 4
- 239000012429 reaction media Substances 0.000 abstract description 4
- 230000029936 alkylation Effects 0.000 abstract description 3
- 238000005804 alkylation reaction Methods 0.000 abstract description 3
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 abstract description 2
- 239000007788 liquid Substances 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- AAXBKJXGVXNSHI-UHFFFAOYSA-N 2-(2-methylprop-2-enoxy)phenol Chemical compound CC(=C)COC1=CC=CC=C1O AAXBKJXGVXNSHI-UHFFFAOYSA-N 0.000 abstract 1
- OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 abstract 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 abstract 1
- 150000008041 alkali metal carbonates Chemical class 0.000 abstract 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 150000001555 benzenes Chemical class 0.000 abstract 1
- 150000004714 phosphonium salts Chemical class 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- 150000005690 diesters Chemical class 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- -1 2,3-dihydro-2,2-dimethyl-7-benzofuranyl Chemical group 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 2
- 229910001948 sodium oxide Inorganic materials 0.000 description 2
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- VEFXTGTZJOWDOF-UHFFFAOYSA-N benzene;hydrate Chemical compound O.C1=CC=CC=C1 VEFXTGTZJOWDOF-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 description 1
- 235000005487 catechin Nutrition 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229950001002 cianidanol Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229930195143 oxyphenol Natural products 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- IPILPUZVTYHGIL-UHFFFAOYSA-M tributyl(methyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](C)(CCCC)CCCC IPILPUZVTYHGIL-UHFFFAOYSA-M 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7819826A FR2434134A1 (fr) | 1978-06-26 | 1978-06-26 | Procede de preparation de l'o-methallyloxyphenol par monoetherification selective de la pyrocatechine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU952102A3 true SU952102A3 (ru) | 1982-08-15 |
Family
ID=9210267
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU792782748A SU952102A3 (ru) | 1978-06-26 | 1979-06-25 | Способ получени 0-металлилоксифенола |
Country Status (26)
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2932458A1 (de) * | 1979-08-10 | 1981-02-26 | Bayer Ag | Herstellung von monoalkylethern von hydroxyphenolen und deren umwandlung zu hydroxycumaranen |
| US4390735A (en) * | 1980-10-22 | 1983-06-28 | Ciba-Geigy Corporation | Process for the preparation of p-allylphenols |
| DE3043230A1 (de) * | 1980-11-15 | 1982-07-08 | Bayer Ag, 5090 Leverkusen | Herstellung von monoalkylaethern von hydroxyphenolen |
| US4465868A (en) * | 1981-07-17 | 1984-08-14 | Otsuka Kagaku Yakuhin Kabushiki Kaisha | Process for preparing o-methallyloxyphenol |
| JPS6013036Y2 (ja) * | 1981-07-29 | 1985-04-25 | 石川島播磨重工業株式会社 | 熱処理炉 |
| IT1151718B (it) * | 1982-04-19 | 1986-12-24 | Brichima Spa | Procedimento per la preparazione del 2,3-diidro-2,2-dimetilbenzofuran-7-olo |
| IT1196002B (it) * | 1984-01-20 | 1988-11-10 | Brichima Spa | Procedimento per la sintesi di o-isopropossifenolo |
| US4639536A (en) * | 1984-08-30 | 1987-01-27 | Union Carbide Corporation | Intermediate, its synthesis, and its use in a process for the preparation of 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran |
| US4618728A (en) * | 1985-02-22 | 1986-10-21 | Fmc Corporation | Water aided catechol etherification |
| US4982012A (en) * | 1987-12-18 | 1991-01-01 | Fmc Corporation | Two phase process for preparing 2-methallyloxyphenol from catechol |
| TW287962B (enrdf_load_stackoverflow) * | 1994-06-13 | 1996-10-11 | Chiyoda Chem Eng Construct Co | |
| FR2772372B1 (fr) * | 1997-12-15 | 2000-05-19 | Rhodia Chimie Sa | Procede de o-alkylation de composes aromatiques hydroxyles |
| CN114307217A (zh) * | 2021-12-30 | 2022-04-12 | 江苏三吉利化工股份有限公司 | 一种呋喃酚废盐中提取邻甲代烯丙氧基苯酚的装置及方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3474171A (en) * | 1964-01-23 | 1969-10-21 | Fmc Corp | 2,2-dimethyl-2,3-dihydrobenzofuranyl-7-n-methylcarbamate |
| US3274260A (en) * | 1964-08-31 | 1966-09-20 | Universal Oil Prod Co | Method for producing monoalkyl ethers of dihydric phenols |
| GB1227144A (enrdf_load_stackoverflow) * | 1967-04-05 | 1971-04-07 | ||
| US3689570A (en) * | 1970-01-14 | 1972-09-05 | Peter S Gradeff | Monoalkylation of unsubstituted dihydric phenols with lower alkyl chlorides using alkali metal carbonates or bicarbonates as a condensing agent |
| US3927118A (en) * | 1973-12-21 | 1975-12-16 | Crown Zellerbach Corp | Process for monoetherification of polyhydric benzenes |
-
1978
- 1978-06-26 FR FR7819826A patent/FR2434134A1/fr active Granted
-
1979
- 1979-06-11 IL IL57539A patent/IL57539A/xx unknown
- 1979-06-12 ES ES481478A patent/ES8107138A1/es not_active Expired
- 1979-06-18 US US06/049,747 patent/US4252985A/en not_active Expired - Lifetime
- 1979-06-21 CH CH582079A patent/CH639055A5/fr not_active IP Right Cessation
- 1979-06-22 CA CA330,364A patent/CA1131255A/en not_active Expired
- 1979-06-22 YU YU1482/79A patent/YU41163B/xx unknown
- 1979-06-25 BG BG044043A patent/BG35033A3/xx unknown
- 1979-06-25 PT PT69815A patent/PT69815A/pt not_active IP Right Cessation
- 1979-06-25 DK DK265779A patent/DK169099B1/da active
- 1979-06-25 LU LU81422A patent/LU81422A1/fr unknown
- 1979-06-25 JP JP8063879A patent/JPS557291A/ja active Granted
- 1979-06-25 BE BE0/195945A patent/BE877243A/xx not_active IP Right Cessation
- 1979-06-25 AT AT0443479A patent/AT371097B/de not_active IP Right Cessation
- 1979-06-25 SE SE7905545A patent/SE448373B/sv not_active IP Right Cessation
- 1979-06-25 PL PL1979216591A patent/PL119189B1/pl unknown
- 1979-06-25 SU SU792782748A patent/SU952102A3/ru active
- 1979-06-26 NL NLAANVRAGE7904969,A patent/NL188468C/xx not_active IP Right Cessation
- 1979-06-26 DE DE19792925763 patent/DE2925763A1/de active Granted
- 1979-06-26 DD DD79213901A patent/DD144534A5/de unknown
- 1979-06-26 BR BR7904035A patent/BR7904035A/pt not_active IP Right Cessation
- 1979-06-26 RO RO7997963A patent/RO77272A/ro unknown
- 1979-06-26 HU HU79PI680A patent/HU185608B/hu not_active IP Right Cessation
- 1979-06-26 IT IT23875/79A patent/IT1121943B/it active
- 1979-08-08 IE IE1176/79A patent/IE49177B1/en not_active IP Right Cessation
- 1979-08-16 ZA ZA793168A patent/ZA793168B/xx unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SU952102A3 (ru) | Способ получени 0-металлилоксифенола | |
| Childs et al. | Preparation of cyanoformates. Crown ether phase transfer catalysis | |
| WO2024139373A1 (zh) | 一种合成咯菌腈中间体2,2-二氟-1,3-苯并二噁茂-4-甲醛的方法 | |
| Matteson | Chlorination of Methaneboronic Acid Derivatives with t-Butyl Hypochlorite | |
| Sato et al. | Copper-catalyzed reaction of grignard reagents with. BETA.-propiolactones: A convenient method for the synthesis of. BETA.-substituted propionic acids. | |
| Ito et al. | Syntheses of. alpha.-chloroketones by reaction of silyl enol ethers with copper (II) chloride and iron (III) chloride | |
| JP2568084B2 (ja) | モノ−若しくはジヒドロキシフルオルアルカンの合成方法 | |
| JP6203431B2 (ja) | 不均一系触媒作用によりアルキル化またはフルオロ、クロロおよびフルオロクロロアルキル化化合物を調製するための方法 | |
| US8779164B2 (en) | Phosphine-based catalysts useful for the telomerization of butadiene | |
| CA1167473A (en) | Process for preparing the mono-methallyl ether of pyrocatechin | |
| JPH0899923A (ja) | 不飽和エーテルの製造方法 | |
| JP2003522743A (ja) | 二重結合の官能化方法 | |
| US20100312019A1 (en) | Preparation of Methyl Fluoroalkyl Ethers | |
| Murray | A high yield procedure for 1-chloro-1-alkynes | |
| Sladek et al. | 3-Fluoropyridyl nickel complexes as useful tools for the selective synthesis of new 2, 4, 5, 6-tetrafluoropyridines: a route complementing the established methods to access fluorinated pyridines | |
| Roling | Nucleophilic substitution reactions on haloazobenzenes | |
| CN110944965A (zh) | 非均相钴催化制备烷基化或氟代烷基化、氯代烷基化、和氟代氯代烷基化化合物的方法 | |
| Masuda et al. | The Hydroboration of 3-Chloro-1-iodo-1-propyne with Dialkylboranes, and Its Application to the Syntheses of Some Geminally Dialkylated Propene Derivatives. | |
| CA1095061A (en) | Cyclic 2-methyl-2,4-dialkoxy-3-buten-1-al-acetals, their preparation and use | |
| Riezebos et al. | Isomerization of safrole to isosafrole by means of iron pentacarbonyl and alkali | |
| RO114323B1 (ro) | Procedeu de obtinere a unor alcooli halogenati | |
| CN109456192A (zh) | 奥拉西坦中间体4-氯乙酰乙酸乙酯的合成方法 | |
| Saegusa et al. | The Acid-catalyzed Reaction of Isocyanide with Oxetane | |
| Ji‐Cheng et al. | Syntheses of a new type of chiral phosphines from glucose | |
| CN118043308A (zh) | 基于偶联反应的键形成方法 |